Novel bis(isobenzofuran)s and their utility in the synthesis of cyclophanes

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dc.contributor.authorThibault, Michelle E.
dc.contributor.authorUniversity of Lethbridge. Faculty of Arts and Science
dc.contributor.supervisorDibble, Peter W.
dc.date.accessioned2007-05-13T20:29:55Z
dc.date.available2007-05-13T20:29:55Z
dc.date.issued2003
dc.degree.levelMasters
dc.descriptionx, 122 leaves : ill. ; 28 cm.en
dc.description.abstractThe synthesis of 1,2-bis(5-isobenzofuranyl)ethene by two routes is described. The first route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(acetal) precursor under basic conditions. However, the synthesis was lengthy with low-yielding steps, which led to it being abandoned. The second route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(oxabicyclic) precursor with 3,6-di(2'-pyridyl)-s-tetrazine. Napththo[1,2-c:5,6-c] difuran and 1,2-bis(5isobenzofuranyl)ethene were used to construct novel cyclophanes by double Diels-Alder reactions with bis(maleimide)s. NMR, AM1 modeling, and X-ray studies of the cyclophanes are discused. Attempts to prepare phenanthro[2,3-c:6,7-c] difuran and its cyclophanes are discussed. None was successful, and investigations were hampered by the inability to obtain sufficient quantities of starting materials. Finally, several suggestions are given for improving the syntheses of 1,2-bis(5- isobenzofuranyl)ethene, phenanthro[2,3-c:6,7-c]difuran, and their cyclophanes. Future directions, such as the functionalization of the double bond of 1,2-bis(5-isobenzofuranyl)ethene, aromatization of the oxabicyclic rings of the cyclophanes, and further X-ray studies are discussed.en
dc.identifier.urihttps://hdl.handle.net/10133/239
dc.language.isoen_USen
dc.publisherLethbridge, Alta. : University of Lethbridge, Faculty of Arts and Science, 2003en
dc.publisher.departmentDepartment of Chemistry and Biochemistry
dc.publisher.facultyArts and Science
dc.relation.ispartofseriesThesis (University of Lethbridge. Faculty of Arts and Science)en
dc.subjectDissertations, Academicen
dc.subjectCyclophanes -- Synthesisen
dc.subjectMacrocyclic compounds -- Synthesisen
dc.subjectAlkenes -- Synthesisen
dc.titleNovel bis(isobenzofuran)s and their utility in the synthesis of cyclophanesen
dc.typeThesisen
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